Sodium Carbonate → (S)-4-(2-chlorophenyl)-3-(3-(3-fluoro-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one

HRID 539113ノート

反応式

HRID 539113 の反応式
Br[C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([N:11]3[C@@H:15]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[Cl:22])[CH2:14][O:13][C:12]3=[O:23])=[N:7][C:6]=12.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.[F:66][C:67]1[CH:72]=[C:71](B2OC(C)(C)C(C)(C)O2)[CH:70]=[CH:69][C:68]=1[C:82]1[N:86]=[CH:85][N:84]([CH2:87][O:88][CH2:89][CH2:90][Si:91]([CH3:94])([CH3:93])[CH3:92])[N:83]=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.CCOC(C)=O.O1CCOCC1>[Cl:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C@H:15]1[CH2:14][O:13][C:12](=[O:23])[N:11]1[C:8]1[CH:9]=[CH:10][N:5]2[N:4]=[CH:3][C:2]([C:71]3[CH:70]=[CH:69][C:68]([C:82]4[N:86]=[CH:85][N:84]([CH2:87][O:88][CH2:89][CH2:90][Si:91]([CH3:93])([CH3:92])[CH3:94])[N:83]=4)=[C:67]([F:66])[CH:72]=3)=[C:6]2[N:7]=1

参加物

9

反応物 4

HCID 10340Sodium CarbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 67034012HCID 67034012、化合物HCID 67035102(S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-chlorophenyl)oxazolidin-2-one

生成物 1

HCID 67034362(S)-4-(2-chlorophenyl)-3-(3-(3-fluoro-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one収率 31%

試薬・触媒・溶媒 4

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

To (S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-chlorophenyl) oxazolidin-2-one (50 mg, 0.13 mmol) were added Pd2 dba3 (5.8 mg, 0.0064 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (7.3 mg, 0.013 mmol), 3-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazole (69 mg, 0.17 mmol), dioxane (1.2 mL) and 2M Na2CO3 (0.2 mL). The reaction was stirred for 2 hours at 80° C. in a sealed tube. After cooling, EtOAc and water were added. The organic phase was washed with brine and dried over MgSO4. The residue was purified by reverse phase chromatography (SP4, 12M, water/CH3CN 90:10 to 0:100, 20 column volumes) to yield (S)-4-(2-chlorophenyl)-3-(3-(3-fluoro-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one (24 mg, 31% yield) as a pale yellow solid.

後処理

  1. temperatureAfter cooling
  2. washThe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. customThe residue was purified by reverse phase chromatography (SP4, 12M, water/CH3CN 90:10 to 0:100, 20 column volumes)

出典と根拠

ORDレコード
ord-b3101ec570e34a8b9186d39dca8f99db
出典データセット
uspto-grants-2014_10
特許番号
US08865726B2

反応ノート

読み込み中…